Second Chances
by LivingInADream95
Summary: What if life really did give people second chances? Rory's life hadn't gone the way she had thought it would. Now, 9 years after the series finale, Rory has been offered a job teaching at Yale. Little does she know, she will be reunited with Jess. Will they get a second shot at love? Rated M for later chapters
1. Chapter 1

**AN:** This is my first Gilmore Girls story. I have wanted to write one for a while now, but never got around to it. This chapter is a lot of background information needed for the story. The story will pick up in later chapters. Let me know what you think!

 **Chapter 1**

Rory pulled up to her new parking space at Yale and took some much-needed deep breaths. When she first got the call asking if she would be interested in teaching, she had no idea what to think. She was both excited and terrified. She hadn't been on this campus in years. She thought of coming back often, but some of the memories were still too raw, even all of these years later. It had been almost a decade ago when she told Logan she couldn't marry him, and the memory of that day still haunts her. It's not that she regrets saying no, but more that she can't stand the thought of having broken his heart, even if saying no was the right thing for both of them. She knew they were both headed in different directions and needed to focus on their new careers, rather than a relationship. She wanted to be a world-renowned journalist, not a housewife. She knew that wouldn't have been a possibility with him, so they parted ways.

Now, here she sits, surrounded by familiar sights. She called this place home for four years, and to her, it will always feel like home. This campus and her mom and Luke's house would always be home to her, no matter where she went or what she did in life. These two places held so many memories for her, so much love, there was no replacing that.

Life hadn't gone exactly as Rory had envisioned it. She pursued a career as a journalist for a few years, before realizing it wasn't for her. After a failed career in journalism, she finally went backpacking with her mom, something they had been talking about doing for as long as she could remember. It had been an amazing experience, but they were both glad to be back home after two months abroad. After that, she had decided to start a blog. She posted about her failed career, her travels, her future dreams, short stories… You name it; she had probably posted about it. To her surprise, the blog was actually pretty popular. She even had advertisers vying for space on her blog to promote their business. She made enough money to get by, and she was happy with her life for the time being.

It was her blog that had piqued the interest of Yale. They contacted her asking if she would consider becoming an English professor and also asked her if she would like to work part-time at their newspaper. Apparently, it had been going downhill in recent years and they thought someone who had been so influential during her time there would be able to help get them back to where they once were. She had told them she would have to take some time to think about it, which really meant she was going to go to her mom's house and make a pro/con list with her. All these years later, and that's still how Rory makes important decisions. It's how she decided to go to Yale, to stop being a journalist, to backpack through Europe, and to begin a blog. Her method hadn't failed her yet.

By the end of the week, she had decided that she would be crazy to turn down an opportunity like this. Not only was it a great decision financially, but also it would get her back into the world she loved so dearly, and secretly missed. She wanted to feel like what she did with her life was making a difference on someone, and what better way to do that than to teach?

She pulled herself from her thoughts long enough to check the time. 8:56. She quickly gathered her things, opened her car door, and sprinted toward her building. She was going to be late on her first day! Not the impression she had hoped to make on her class. By the time she had finally made it, which happened to be one minute before class started, she was out of breath and sweaty. As she looked up, she saw fifty pairs of eyes looking back at her. She smiled a weak smile and apologized for her disheveled appearance before breaking the ice with a joke.

When the class laughed and stopped staring at her like she had a bird in her hair, she breathed a sigh of relief and took her laptop out of the bag. She told herself everything was going to be okay. English was her passion and she would be able to give a killer lecture, sweat stains or not. It wasn't until she had connected her laptop and pulled her lecture presentation up that she saw him. There, sitting in the back row, was Jess Mariano. Rory felt faint. She hadn't seen Jess since the incident. She hadn't forgotten their kiss. In fact, it was one of the many reasons why she had said no to Logan. As much as she told herself it was because of her career, deep down she knew it was because she would always be in love with Jess.

She had to take some more deep breaths to calm herself down enough to begin the lecture. A few breaths and a mental pep talk later, and she was ready to begin. She introduced herself, did some icebreaker activities, went through the syllabus, and told the class she would see them next Monday.

As she was packing up her stuff, she heard footsteps approaching her. She looked up to see Jess, smiling that trademark crooked smile of his.


	2. Chapter 2

**AN:** Thank you to everyone who read the last chapter and everyone who reviewed or added this story to their alerts. This chapter was a bit of a struggle to write, so hopefully it was worth it. It took me writing a few versions to settle on one I liked, so I apologize if there are any minor mistakes. I wanted to get this chapter out before I had time to overthink it again

 **Chapter 2**

"Jess."

It took everything Rory had in her just to get his name out. It had been so long since she last saw him, but the emotions- the regret, the longing- they were all still there; raw and demanding to be felt. It left her speechless, something only he had the power to do anymore.

"It's been a while," he replied

"Too long."

They both stood there awkwardly for a few seconds, both too caught up in their own thoughts to think of something to say to the other person. Being this close to Jess again was causing Rory's brain to short-circuit. All those years of reading countless novels, writing countless articles, and one guy had the power to turn her brain to mush.

"You're back," she finally said.

"I'm back."

"For good?" she asked, trying to keep the desperation out of her voice.

"For good," he replied with a grin.

Rory closed the space between them and pulled him in for a hug. He hugged her back, squeezing her tightly against him. They stayed like this for a while, neither wanting to let go and risk that this might all be just a dream.

It was Rory who finally brought them back to reality, pulling back a little so she could look at him. She smiled and asked him how long he'd been back.

"Not long," he said. "I've been staying with Luke and Lorelai for the past few weeks while I look for a place to stay."

"You're really back?" she was having a hard time believing it. This was something she had wanted for so long, to see Jess again, to make things right, and now she might actually get the chance. She might get her second chance.

He laughed. "Yes, I'm really back. Jeez, did you hit your head on the way here Gilmore?"

Now it was her turn to laugh. "No, it's just… A lot to take in. You being back."

"Well you better start taking it in, because I'm not going away anytime soon. Besides, you're stuck seeing me in class every week. Don't think you can get rid of me that easy."

"Am I the only one who sees the irony in this situation?" Rory couldn't help herself, seeing him here today, as one of her students, it reminded her of the time Luke asked her to tutor Jess. To say he actually needed a tutor was absurd, he was smarter than anyone ever gave him credit for; he just had never applied himself because he didn't see the point. How times have changed.

"Maybe I'll actually study this time," he said with a wink. "I may even pass the class with the help of this great tutor I had in high school."

They both laughed. It was like old times, the easy banter between them. Rory was grateful for this, but her regret over the past still loomed over her. She needed to apologize, to explain herself, but she needed to figure out the right way to say it.

"Do you have any other classes today?" he asked.

"Nope, this is was my only class today."

"Well, if you're free, we should go grab a coffee and catch up… Give me the chance to corrupt the innocent Rory Gilmore once more."

She tried to cover the blush she felt burning her cheeks, but it was no use.

"I'd like that," she finally said.

"Good. You lead the way, this is your old stomping grounds after all."

"I know just the place," she said with a smile.

They headed out to Rory's car and she drove the to her favourite local spot. It was a coffee shop/diner combo, which was the best of both worlds in her opinion. It wasn't far off campus, but far enough that it wasn't too crowded. It had been where she got her coffee fix when she didn't have time to go to Luke's. Thinking about Luke got her wondering if her mother had known about Jess being in her class all along. She had a sneaking suspicion that her mom had been aware of it the whole time. The situation screamed Lorelai Gilmore. She rolled her eyes. Leave it to her mother to keep something this significant a surprise to Rory.

They spent the five-minute drive in silence, both wrapped up in their own thoughts once again. When Rory pulled into the parking lot and turned off the car, she found Jess looking at her and the building skeptically.

"What? You haven't even been inside yet, you can't already hate the place," she said. "This place has amazing coffee. It even has fantastic diner food. We both know you love diner food."

"Diner food yes, coffee shop food, no. I find it hard to believe that this place serves diner food. Look at it. It's a coffee shop," he said in exasperation.

"Looks can be deceiving Mariano."

"Funny, sounds like something you used to say to your mom about me," he retorted with a smirk.

"Well was I wrong? There's more to you than meets the eye, Jess. You put up this 'bad boy' front, but deep down you're an intelligent, and sometimes even caring, man. You can deny that all you want, but we both know I'm right. So why don't you just trust me on this one too. Have a little faith Mariano. Life is full of surprises."

"Okay, okay… If it will shut you up, I'll go in."

She smiled. She always did know how to get Jess to give in and give things a shot.

"But if this place is the douchy coffee shop it looks like, you owe me big time Gilmore."

"Deal, now get out of the car. I'm starving."

"You're always starving."

They headed inside and grabbed a booth by the window. When the waitress came over with the menus, Rory ordered a coffee before the woman even had a chance to ask if they wanted anything to drink. Jess smirked, ordering himself a coffee as well when the waitress asked if he'd like anything.

"Nice to see you still run on caffeine and junk food," he said sarcastically after the waitress left to get their coffees.

She gave him a playful punch on the arm.

"Hey!" he exclaimed, feigning injury. "I'm not criticizing, I'm just saying it might be easier to just put the coffee into an IV and carry it around with you."

They both laughed.

"You know, you might be onto something," she said.

"Please don't," he replied. "I'd rather not be the one responsible for you going into cardiac arrest. I wouldn't be able to withstand your mother's wrath."

"Alright, alright, I'll stick to drinking coffee the old fashioned way."

"Good."

"Party pooper," she muttered.

He gave her a glare, "well excuse me for wanting my friend to stay alive long enough to see next week."

"Apology accepted," she said with a grin.

He rolled his eyes at her and took a sip from the steaming cup of coffee the waitress had brought over. Rory took a large gulp of coffee, reveling in the much needed caffeine jolt after the morning she had had.

She looked up at him expectantly, "so, was I right?"

"About what?"

"The coffee… and the fact that this place isn't 'douchy'."

"Too soon to tell. The coffee is good, but I haven't even opened the menu. Can't make a proper verdict without the food, now can I?"

"I guess you're right. Food is important, especially greasy diner food."

Jess laughed, "boy you and Lorelai must drive my uncle crazy."

She smiled, "yeah, he still complains about how I got my mother's eating habits."

"Sounds like him."

"It's funny, that's one of the things I like most about him. Sure, sometimes I wish we could just have our coffee and greasy food without a lecture, but it's nice to know he cares. You know?"

"Yeah, Luke's good for that. Caring. He cares more about me than my mother ever did, that's for sure."

"He talks about you a lot. I think he missed you."

"I can't picture Luke missing someone."

"He doesn't show it, but deep down, he's just a big teddy bear."

Jess burst out laughing, "I'm definitely telling him you said that."

Rory leaned forward and clamped her hands over his mouth to stop the laughter.

"You will do no such thing," she said sternly. "We do not offend the man in charge of the good food."

"Hmm, you may have a point."

"Focus, you need to look at your menu so we can order before I die right here at this very table."

"You know, if this whole English teacher thing doesn't work out, you may want to consider a career on Broadway. Waiting ten more minutes to eat will not kill you."

"It might."

Jess opened up his menu, deciding it was better to concede than continue a battle he was bound to lose, besides, he was also pretty hungry. Once he had decided what he wanted, Rory wasted no time signalling the waitress back to their table so they could place their order.

"So what made you decide to go to Yale?"

"Honestly, I just needed a change of pace. The New York author life was great for a while, but it got old quick. I figured the best thing to do would be to stay with Luke while I figured out my next move. Luke was mentioning the idea of taking some classes while I figure things out, and I thought why not." Jess laughed, "if someone would have told me ten years ago that this is where I was going to end up, I would have thought they were nuts, but here we are."

Rory smiled, "Jess, that's great! You'll love Yale."

"Thanks," he replied with a smile. "Speaking of big changes, what brings you back to Yale? I thought you wanted to be the next Christiane Amanpour."

"I used to… I spent a few years working as a journalist and pursuing that dream, but then I realized it wasn't for me. Like you said, it was great for a while, but eventually I just needed a change of scenery. After I quit my job, I went back to live with Mom and Luke for a while. Mom convinced me that it was the perfect time to finally go backpacking through Europe. When we got back, I actually started a blog. It made enough money to get by, and I enjoyed doing it. Then, out of the blue, Yale called and asked if I would consider teaching an English class and working on the paper. I couldn't pass that up, so here we are."

"It's funny to think how much things can change in nine years," Jess said thoughtfully.

"And yet, some things stay the same," Rory responded, thinking about their friendship and her love for Jess.

Jess nodded in agreement.

They spent the rest of their lunch exchanging stories about their lives over the past nine years and making small talk, both enjoying the other's company.


End file.
